For parents of young children and adolescents, the digital age has introduced many new challenges, including excessive screen time, inappropriate online content, cyber predators, and cyberbullying. To address these challenges, many parents rely on numerous parental control solutions on different platforms, including parental control network devices and software applications on mobile devices and laptops. While these parental control solutions may help digital parenting, they may also introduce serious security and privacy risks to children and parents, due to their elevated privileges and having access to a significant amount of privacy-sensitive data. In recent years, attacks and security flaws concerning this type of applications have flourished, however no systematic study for the security and privacy of these parental control solutions has been carried out to date. In this thesis, we present an experimental framework for systematically evaluating security and privacy issues in parental control software and hardware solutions. Using the developed framework, we provide the first comprehensive study of parental control solutions on multiple platforms including network devices, mobile apps, Windows applications and web extensions. We analyze a representative dataset of each type of solution and build a security and privacy state-of-the-art of each environment. Our analysis uncovers pervasive security and privacy issues that can lead to leakage of private information, and/or allow an adversary to fully control the parental control solution, and thereby may directly aid cyberbullying and cyber predators.